(S)-5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-one

Base Information

Chemical Name:(S)-5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-one
CAS No.:332386-78-4
Molecular Formula:C₅₀H₄₂O₇
Molecular Weight:754.879
Hs Code.:

Synonyms:(S)-5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-one

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Chemical Property of (S)-5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-one

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Technology Process of (S)-5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-one

There total 11 articles about (S)-5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 332386-70-6
(+)-(2S,3R)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol

: 332386-78-4
(S)-5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃;
DOI:10.1021/ol000394z

Reference yield:

: 332386-67-1
ethyl (E)-3,4,5-tris(benzyloxy)cinnamate

: 332386-78-4
(S)-5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-one

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / DIBAL / tetrahydrofuran; toluene / 2 h / -78 - 20 °C

2: 463 mg / H₂SO₄*SiO₂ / CS₂; CH₂Cl₂ / 3 h / 20 °C

3: 428 mg / imidazole / dimethylformamide / 20 °C

4: AD-mix-α; CH3SO2NH2; H2O / 2-methyl-propan-2-ol; CH2Cl2 / 0 °C

5: 318 mg / TBAF / tetrahydrofuran / 4 h / 20 °C

6: PPTS / CH₂Cl₂ / 20 °C

7: CH(OEt)3; PPTS / 1,2-dichloro-ethane / 60 °C

8: K₂CO₃ / methanol

9: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With 1H-imidazole; AD-mix-α; methanesulfonamide; sulfuric acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; orthoformic acid triethyl ester; In tetrahydrofuran; methanol; carbon disulfide; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 4: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ol000394z

Reference yield:

: 79831-88-2
3,4,5-tribenzyloxybenzyl alcohol

: 332386-78-4
(S)-5,7-Bis-benzyloxy-2-(3,4,5-tris-benzyloxy-phenyl)-chroman-3-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: PDC / CH₂Cl₂ / 20 °C

1.2: 91 percent / NaH / tetrahydrofuran / 2 h / 20 °C

2.1: 95 percent / DIBAL / tetrahydrofuran; toluene / 2 h / -78 - 20 °C

3.1: 463 mg / H₂SO₄*SiO₂ / CS₂; CH₂Cl₂ / 3 h / 20 °C

4.1: 428 mg / imidazole / dimethylformamide / 20 °C

5.1: AD-mix-α; CH3SO2NH2; H2O / 2-methyl-propan-2-ol; CH2Cl2 / 0 °C

6.1: 318 mg / TBAF / tetrahydrofuran / 4 h / 20 °C

7.1: PPTS / CH₂Cl₂ / 20 °C

8.1: CH(OEt)3; PPTS / 1,2-dichloro-ethane / 60 °C

9.1: K₂CO₃ / methanol

10.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With 1H-imidazole; AD-mix-α; dipyridinium dichromate; methanesulfonamide; sulfuric acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; orthoformic acid triethyl ester; In tetrahydrofuran; methanol; carbon disulfide; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 5.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ol000394z